Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Patent
1995-06-06
1998-01-06
Kunz, Gary L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
536 289, A61K 3170, C07H 1923
Patent
active
057054908
ABSTRACT:
This invention relates to novel polysubstituted benzimidazoles and compositions and their use in the treatment of viral infections. The polysubstituted benzimidazoles and compositions of the present invention exhibit antiviral properties against viruses of the herpes family, particularly human cytomegalovirus (HCMV) and herpes simplex viruses (HSV).
REFERENCES:
patent: 2860131 (1958-11-01), Folkers et al.
patent: 2935508 (1960-05-01), Shunk et al.
patent: 3037980 (1962-06-01), Hitchings et al.
patent: 3311628 (1967-03-01), Partyka
patent: 3631036 (1971-12-01), Kim et al.
patent: 3655901 (1972-04-01), Jensen et al.
patent: 3686411 (1972-08-01), Frick et al.
patent: 3817982 (1974-06-01), Verheyden et al.
patent: 3867386 (1975-02-01), Kim et al.
patent: 3914310 (1975-10-01), Frick et al.
patent: 3962211 (1976-06-01), Townsend et al.
patent: 4199574 (1980-04-01), Schaeffer
patent: 4229453 (1980-10-01), Roth et al.
patent: 4482708 (1984-11-01), Nguyen
patent: 4596798 (1986-06-01), Shipman, Jr. et al.
patent: 4777129 (1988-10-01), Dattagupta et al.
patent: 4892865 (1990-01-01), Townsend et al.
patent: 4927830 (1990-05-01), Townsend et al.
patent: 4968686 (1990-11-01), Townsend et al.
patent: 5077407 (1991-12-01), Sih
patent: 5149700 (1992-09-01), Ellingboe et al.
patent: 5248672 (1993-09-01), Townsend et al.
patent: 5360795 (1994-11-01), Townsend et al.
Martin et al, J. Pharm. Sci. 76:180-184, 1987.
Casida et al. Biochem. Pharm. 13:637-644, 1966.
Blythin et al., Chemical Abstracts 105:6481r, 1986 (J. Med. Chem., 1986, vol. 29, No. 6, p. 1099).
Lopyrev et al., Chemical Abstracts 101:6202t, 1984 (Deposited document 1982, VINITI 6097-82, Russian).
Postovskii et al., Chemical Abstracts 83:164074, 1975 (Khim. Geterotsikl. Soedin., 1975, vol. 7, pp. 987-989).
Uchida et al., Chemical Abstracts 107:39827c, 1987 (Japanese Kokai JP 62-71978, 1987).
Vivarelli et al., Chemical Abstracts 84:12717g, 1976 (Gazz. Chim. Ital., 1975, vol. 105, No. 7-8, pp. 801-806).
Bergstrom, D., et al., "Antiviral Activity of C-5 Substituted Tubercidin Analogues", J. Med. Chem., vol. 27, pp. 285-292 (1984).
DeClercq, E., et al., "Antirhinovirus Activity of Purine Nucleoside Analogs", Antimicrob. Agents and Chemother., vol. 29, No. 3, pp. 482-487 (Mar. 1986).
DeClercq, E., et al., "Nucleic Acid Related Compounds. 51. Synthesis and Biological Properties of Sugar-Modified Analogues of the Nucleoside Antibiotics Tubercidin, Toyocamycin, Sangivamycin, and Formycin", J. Med. Chem., vol. 30, pp. 481-586 (1987).
Devivar, R.V., et al., "The Formation of an Unusual Product During Studies on the Diazotization of Certain 2-Aminobenzimidazoles", Abstracts of Papers, Part II, 199th ACS National Meeting, Americal Chemical Society (Boston, Massachusettes, Apr. 22-27, 1990), Abstract No. MEDI 24.
Drach, J., et al., "Tritiated Thymidine Incorporation Does Not Measure DNA Synthesis in Ribavirin-Treated Human Cells", Science, vol. 212., pp. 549-551 (1981).
Drach, J.C., et al., "Comparison of the Activity of Tubercidin Analogs Against Herpesviruses", abstract presented at 28th ICAAC, Los Angeles, CA on 25 Oct. 1988, 1 page total. 4-Pyrimidiylhydrazones, a 2-Bis(methylthio)methyleneaminopyrrole-3-carbonitrile, and a I), vol. 16, pp. 1921-1929 (1974).
Gadler, H., "Nucleic Acid Hybridization for Measurement of Effects of Antiviral Compounds on Human Cytomegalovirus DNA Replication", Antimicrob. Agents and Chemother., vol. 24, pp. 370-374 (1983).
Gupta, P.K., et al., "Synthesis, Cytotoxicity, and Antiviral Activity of Antibiotics Tubercidin, Toyocamycin, and Sangivamycin", J. Med. Chem., vol. 32, No. 2, pp. 402-408 (1989).
Hansske, F., et al., "2' and 3'-Ketonucleosides and Their Arabino and Xylo Reduction Products", Tetrahedron, vol. 40, No. 1, pp. 125-135 (1984).
Hayflick, B., "Chapter 10: Screening Tissue Cultures for Mycoplasma Infections", in Tissue Culture: Methods and Applications (Academic Press, 1973), pp. 722-728.
Jain, T.C., et al., "Reactions of 2-Acyloxyisobutyryl Halides with Nucleosides. III. Reactions of Tubercidin and Formycin", J. Org. Chem., vol. 38, No. 18, pp. 3179-3186 (1973).
Joseph et al., "Dialkylamination by Means of Dimethylformamide (DMF) 2-Dimethylaminobenzimidazoles (1)", J. Heterocyclic Chem., vol. 3(1), pp. 107-108 (1966). (Additional abstract attached).
Maruyama, T., et al., "Pyrrolopyrimidine Nucleosides. 18. Synthesis and Chemotherapeutic Activity of xamide (3'-Deoxysangivamycin) and xamide (2'-Deoxysangivamycin)", J. Med. Chem., vol. 26, pp. 25-29 (1983).
Mitsuya, H., et al., "3'-Azido-3'-deoxythimidine (BW A509U): An Antiviral Agent that Inhibits the Infectivity and Cytopathic Effect of Human T-Lymphotropic Virus Type III/Lymphadenopathy-Associated Vitus in Vitro", Proc. Natl. Acad. Sci., vol. 82, pp. 7096-7100 (Oct. 1985).
Mitsuya, H., et al., "Inhibition of the In Vitro Infectivity and Cytopathic Effect of Human T-Lymphotropic Virus Type III/Lymphadenopathy-Associated Virus (HTLV-III/LAW) by 2',3'-dideoxynucleosides", Proc. Natl. Acad. Sci., vol. 83, pp. 1911-1915 (Mar. 1986).
Nassiri, M.R., et al., "Kinetic Assessment by Flow Cytometry of the Effect of Two New Antiviral Drugs on the Cell Cycle", abstract presented at 3rd Annual Meeting Clinical Applications of Cytometry, Charleston, SC, 14-17 Sep. 1988, 1 page total.
N'Diaye et al., "Synthese et etude parasitologique de (1987) (including English language abstract).
Pudio, J.S., et al., "Synthesis and Antiviral Activity of Certain 4-and Med. Chem., vol. 31, No. 11, pp. 2086-2092 (1988).
Ramasamy, K., et al., "Total Synthesis of 2'-Deoxytoyocamycin, 2'-Deoxysangivamycin and Related Pyrrole Precursors Prepared by the Stereospecific Sodium Salt Glycosylation Procedure", Abstracts of Papers, 192th ACS National Meeting, American Chemical Society (Anaheim, California, Sep. 7-12, 1986), Abstract No. 65, 2 pages total.
Ricci et al., "Reattivita nucleofila di alcuni 2-cloro-5(6)-X-benzimidazoli", Bollettino, vol. 23, pp. 409-413 (1965) (English language abstract attached).
Robins, M.J., et al., "Nucleic Acid Related Compounds. 24. Transformation of Tubercidin 2',3'-O-orthoacetate into Halo, Deoxy, Epoxide, and Unsaturated Sugar Nucleosides", Can. J. Chem., vol. 55, pp. 1251-1259 (1977).
Robins, M.J., et al., "A Mild Conversion of Vincinal Diols to Alkenes. Efficient Transformation of Ribonucleosides into 2'-ene and 2',3'-dideoxynucleosides", Tetrahedron Letters, vol. 25, No. 4, pp. 367-370 (1984).
Saluja, S., et al., "Synthesis and Antiviral Activity of Certain 2-Substituted 4,5,6,7-Tetrachlorobenzimidazole Acyclic Nucleosides", Abstracts of Papers, Part II, 199th ACS National Meeting, Americal Chemical Society (Boston, Massachusettes, Apr. 22-27, 1990), Abstract No. MEDI 22.
Saxena, N.K., et al., "Synthesis and Antiviral Activity of Certain 4-Substituted and 2,4-Disubstituted vol. 31, No. 8, pp. 1501-1506 (1988).
Shipman, C., Jr., "Antiviral Activity of Arabinosyladenine and Arabinosylhypoxanthine in Herpes Simplex Virus-Infected KB Cells: Selective Inhibition of Viral Deoxyribonucleic Acid Synthesis in Synchronized Suspension Cultures", Antimicrob. Agents and Chemother., vol. 9, No. 1, pp. 120-127 (Jan. 1976).
Shipman, C., Jr., "Evaluation of 4-(2-Hydroxyethyl)-1-piperazineethanesulfonic Acid (HEPES) as a Tissue Culture Buffer", Proc. Soc. Exp. Biol. Med., vol. 120, pp. 305-310 (1969).
Sigma Chemical Company Catalog, St. Louis, MO., 1984, p. 898 lists tubercidin.
Smith, C.M., et al., "Inhibitors of Hypoxanthine Metabolism in Ehrlich Ascites Tumor Cells In Vitro", Cancer Treatment Reports, vol. 60, No. 10, pp. 1567-1582 (Oct. 1976).
Tamm, I., et al., "Inhibition of Influenza and Mumps Virus Multiplication by 4,5,6-(or 5,6,7-) Trichloro-1-.beta.-D-Ribofuranosylbenzimidazole", Science, vol. 120, pp. 847-848, (Nov. 1954).
Tolman, R.L., et al., "Pyrrolopyrimidine Nucleosides. III. The Total Synthesis of Toyacamycin, Sangivamycin, Tubercidin, and Related Derivatives", J. Amer. Chem. Soc., vol. 91, No. 8, pp. 2102-2108 (Apr. 1969).
Townsend, L.B., et al., "Benzimidazole Nucleosides, Nucleotides, and Related Derivatives", Chemical Reviews, vol. 70, pp. 389-438 (197
Drach John C.
Townsend Leroy B.
Kunz Gary L.
The Regents of the University of Michigan
LandOfFree
Polysubstituted benzimidazoles as antiviral agents does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Polysubstituted benzimidazoles as antiviral agents, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Polysubstituted benzimidazoles as antiviral agents will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2329274